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Jason Earles Shares the Advice He Would Give Himself in the Early Days of “Hannah Montana” (Exclusive)

‘Hannah Montana’ first aired on the Disney Channel on March 24, 2006, introducing us to Earles' character, Jackson Stewart

Jason Earles.
Credit: Disney Channel/Kobal/Shutterstock; Michael Buckner/Variety via Getty

NEED TO KNOW

  • On March 23, Jason Earles made an appearance at the Hannah Montana 20th Anniversary special premiere at El Capitan Theatre in Los Angeles
  • Former cast members, including Miley Cyrus, Moises Arias, Cody Linley, and Ashley Maria Perez de Tangle were also in attendance
  • During the event, the 48-year-old actor looked back on his time on set and shared the advice he would offer his younger self today

At a nostalgic reunion two decades in the making, Jason Earles revisited a defining era of his career.

On Monday, March 23, the 48-year-old actor, who played Jackson Stewart on the show, made an appearance at the Hannah Montana 20th Anniversary special premiere in Los Angeles, instantly bringing back memories by wearing his signature red Rico’s T-shirt. The playful nod to his on-screen past reflected just how deeply the show still resonates with fans and with Earles himself.

Looking back on the whirlwind that started it all, he reflected on what advice he’d offer his younger self: “I think just… settle in sooner,” Earles tells PEOPLE exclusively.

Jason Earles, Miley Cyrus, and Billy Ray Cyrus.Credit: Dean Hendler/Disney Channel/Kobal/Shutterstock
Jason Earles, Miley Cyrus, and Billy Ray Cyrus.
Credit: Dean Hendler/Disney Channel/Kobal/Shutterstock

During his early days filming Hannah Montana, Earles admits he was far from at ease.

“I was really nervous about fitting in and if my humor was the right sense of humor for the show and if I was… approaching it as an actor the right way,” he admits. “I think I was just not as confident as early as I could have been.”

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Billy Ray Cyrus and Jason Earles.Credit: Disney Channel/Kobal/Shutterstock
Billy Ray Cyrus and Jason Earles.
Credit: Disney Channel/Kobal/Shutterstock

Part of that uncertainty stemmed from a secret he had been carrying behind the scenes. On a recent episode of his new podcast, Best of Both Our Worlds, Earles revealed he “lied” about his age when auditioning.

“I was desperately afraid that I was going to be fired and recast because I had a big secret,” he admitted while speaking candidly with the show’s alums, director Shannon Flynn and writer-producer Douglas Danger Lieblein. “When I auditioned for the show, I lied to them and told them I was 18 years old.”

In truth, Earles was 28 at the time, already navigating adulthood while trying to portray a teenager.

Jason Earles at the 'Hannah Montana' 20th Anniversary special.Credit: Julian Hamilton/FilmMagic)
Jason Earles at the 'Hannah Montana' 20th Anniversary special.
Credit: Julian Hamilton/FilmMagic)

In hindsight, Earles says he wishes he had approached the experience with more ease. Reflecting on the journey, he now believes a calmer mindset would have made those early days more enjoyable, noting that he would tell himself “it’s going to be OK. The show's going to be good. You'll be fine.”

Since his Disney Channel breakout, Earles has continued working steadily, with appearances in TV shows like Still Standing and films like National Treasure, Space Buddies and Gordon Glass.

Off-screen, Earles married Katie Drysen in 2017, marking another chapter in a life that has evolved far beyond the Malibu beach house.

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